Staff Product Manager, AI Assistant

Ready to make a serious impact? Millions of people already rely on Calendly, and we’re still in the midst of exciting product growth — it’s a fantastic time to join us. Everything you’ll work on here will accelerate your career to the next level. If you want to learn, grow, and do the best work of your life alongside the best people you’ve ever worked with, then we hope you’ll consider allowing Calendly to be a part of your professional journey.

This is a hybrid position located in the Bay Area; the expectation is to go into the San Francisco office 2 times per week. Calendly is used by more than 20 million people to take the work out of scheduling. We're now building the layer that does the work around the meeting too: the prep before it, the follow-up after it, and the next step a professional would otherwise do manually. This role owns the assistant that surfaces and drafts those actions, and the quality that makes people trust them.

Responsibilities

• Understand the work that surrounds meetings for our users: what they're trying to accomplish, where they lose time, and which of those problems are worth solving and how to solve them simply enough that users feel the help without the overhead.
• Turn those problems into an assistant that helps at the right moments.
• Earn enough trust in the assistant's output that users are willing to hand it more autonomy over time, letting it act without reviewing every step.
• Ship fast and learn in the open: get real versions in front of users, watch how they respond, and iterate quickly.

Requirements

• A minimum of 8-10 years of varied PM experience across both startups and scaled companies; bonus points if you've been a founder.
• Experience with assistant or agent products, or with AI-generated content where voice and tone mattered.
• Real taste for AI output quality.
• Keen product sense and UX design experience, with deep empathy for customers and a drive to build delightful, frictionless experiences.
• Experience building 0-to-1 products.
• The ability to work in our San Francisco office 1-3 times per week.
• Authorized to work lawfully in the United States of America, as Calendly does not engage in immigration sponsorship at this time.

If you are an individual with a disability and would like to request a reasonable accommodation as part of the application or recruiting process, please contact us at recruiting@calendly.com.

Pay

The ranges listed below are the expected annual base salary for this role, subject to change. Calendly takes a number of factors into consideration when determining an employee’s starting salary, including relevant experience, relevant skills sets, interview performance, location/metropolitan area, and internal pay equity. Base salary is just one component of Calendly’s total rewards package.

• Tier 1: $180,000 - $220,000 (San Francisco, CA, San Jose, CA, New York City, NY)
• Tier 2: $165,000 - $200,000 (Chicago, IL, Austin, TX, Denver, CO, Boston, MA, Washington D.C., Philadelphia, PA, Portland, OR, Seattle, WA, Miami, FL, and all other cities in CA)
• Tier 3: $150,000 - $185,000 (All other locations not in Tier 1 or Tier 2)

All full-time (30 hours/week) employees are also eligible for equity awards, a Top Performer Bonus program (or Sales incentive for eligible roles), and competitive benefits. This role may require occasional travel for company events, team collaboration, or offsites.

Schedule

• Hybrid position: 1-3 days per week in the San Francisco office.
• Full-time: 30+ hours per week.